Synthesis of secondary E-allylamines and β-aminophosphorylated compounds from β-functionalized enamines derived from phosphonium salts, phosphine oxides and phosphonates

Article abstract of DOI:10.1016/0040-4020(96)00498-X

A simple and stereoselective synthesis of secondary E-allylamines 1 and 20 from functionalized enamines derived from phosphine oxides 8, phosphonium salts 11 and phosphonates 12 is reported. Phosphorus compounds 8, 11 and 12 are obtained by amine addition to phosphorylated allenes 7, 10 and phosphonium salts 9. Reduction of enamines 8 and 12 with hydrides leads to the formation of β-amino phosphine oxides 13 and phoshonates 14. Allylamines 1, 20 and β-aminophosphorylated derivatives 13 and 14 can also be obtained in 'one pot' reaction from allenes 7, 10 and phosphonium salus 9 without the isolation and purification of enamines 8, 11 and 12.